30 Day OTP Challenge
by thebenniebabyninja
Summary: This will be a collection of Oneshot stories for my 30 day OTP challenge on deviantart. If you'd like to see the art associtated with it please visit my profile for the link! Thanks! Rated T for language.
1. Day One: Holding Hands

Edward Kenway sat on top of the windmill in Kingston playing nervously with the cuff of his sleeve. The sun began to set and he knew Kidd would be there soon. He flicked his wrist blade out, checking his appearance in the reflection of the blade. He licked his fingers and pulled at his hair in an attempt to fix a piece of hair that was sticking up off his forehead. He finches slightly when he hears the soft thump next to him, alerting him of his companion's arrival. "Wouldn't ya prefer meeting in a pub?" She mocks attempting at a welsh accent. What a wisecracker. He rolls his eyes but smiles, remember back on the last time the two met up on this windmill. Edward glances over at the smirking face of James Kidd. Or is it Mary Read now?

He looks his partner up and down, Kidd's smirk growing wider the longer he stares. She crosses her arms over her chest and taps her foot softly against the roof, "Now what was it ya wanted, that ya brought me all the way to bloody Kingston, to talk about?" Edward takes a deep breath trying to steady the quick beat of his heart. "Sit down Kidd." The words come out shaky and he can't help but to curse under his breath. She plops down next to him and pulls out her pipe. "This can't be good..." She trails off and lights her pipe, taking a long drag. He can't help but to watch her lips around the end of the pipe.

He wets his own lips and begns, "Mary-" He's quickly cut off by the sound of her hidden blade, he looks down and her knife is pointed dangerously at his crotch. He rolls his eyes and pushes her hand away, "Your secret is safe with me lass, who's going to hear us all the way up here anyway?" Her blade retracts into its sheath, she takes another drag off the pipe and waves at him to continue. "Mary how long have we known each other?"

She quirks a scarred eyebrow up and blows a cloud of smoke from the corner of her mouth. "Five years or so, why?" Edward scrubs his face with his hands, conflicting feelings thrown around in his head, Jaysus, five years. Everything's about to turn to shite if she doesn't feel the same. He buries his head in his arms and releases a pained groan from the back of his throat. He's obviously gotten her attention now, she's putting out her pipe and turns her body to face towards her friend. "Kenway, what's wrong?"

He props his chin up against his arms, watching as the last bit of sun trickled behind the horizon, bathing his surroundings in darkness. He sighs again and she places a hand to his shoulder, squeezing gently in a means of comfort. He squeezes his eyes shut and squeeks out, "Five years is quite a long time." James replies with a soft, "Aye." And she drops her hand away from his shoulder, he frowns wishing for even the smallest bit of contact. He scoots a bit closer. She obviously noticed but for some odd reason didn't say anything about it. "In those five years I've not heard hide nor hair of any man in your life. Do you prefer women?"

She chuckles but quickly looks away, it was only a fraction of a second but he saw the pain hiding behind her eyes. "Aye, I've been with women but I prefer cock." He can't keep the smile from his face, "But." His grin is quickly replaced with a frown, But what? But is never a good sign. She sighs and runs a hand through the hair sprouting from her bandana. The two grow quiet, listening to the quiet chirping coming from the crickets below.

"I had a husband, Kenway, as you have a wife." His eyes widen and he can't stop his mouth fast enough, "How could anyone leave a beautiful lass as yourself?" Her face contorts into that of pain, tears threaten to spill from her eyes but she bites her lip and they recede. "I don't believe he left intentionally, Edward." His eyes widen upon the use of his first name, she's never called him by his first name. "We met in the Navy and settled down together a few years after he found out my secret." He nods and she pauses, no doubt hoping to steady her quivering voice.

"A year after we retired he was asked to re-enlist. He died at sea not three months later." Edward couldn't help himself from latching onto her shoulder, she tenses and leans away from his touch. His heart feels heavy in his chest as she continues, "I haven't been with a man since he passed and that was nearly seven years ago."

Edward bites at his cheek, knowing all to well what it was like to miss a spouse. James hides her face into her knees, her shoulders shaking a bit as she, as he assumed, began to cry. He feels that tightness in his chest again, heart breaking for being the one to cause Mary to relive those memories. He squeezes her shoulder reassuringly and she sits back up wiping a tear from the corner of her eye. "Kenway, I know you didn't just come up here for me to spill my guts to ya. Now what did ya want?" He straightens himself, was he sure about doing this? He clears his throat again and speaks, "Actually that's exactly what I wanted." She quirks a brow obviously confused.

Edward's hand finds her's and he links their fingers together. She looks down at their hands and tries to pull away. His grip tightens and his other hand finds her cheek and she flicks her eyes up into his hopeful ones, "Mary, I know that we don't always see eye to eye however I know we both enjoy each other's company. Lately I've been finding myself thinking of you as more than a friend. Mary Read, I think I'm in love with you." She pulls her hand away from his and he backs away hurt, "Oh posh Edward, you're only thinking that because ya miss you're wife."

He sighs and rubs the bridge of his nose, "Aye, I miss her. But I don't think she misses me, we're done Mary, there's nothing for me to return to." James stands and Edward's heart drops, "Mary, don't go..." She crouches down in front of him and places a hand to his cheek. "Edward I love ya too, but I can't do this." He grabs her hand that was resting on his cheek and, for the first time, he cries in front of her. She sighs and brushes the tear away with her thumb, "Kenway-"

She's cut off when he places his lips over her's in a hard wanton kiss. His heart races when she begins to respond, he feels her smile into the kiss and she wraps her arms around his neck. He flips their position so her back is being pushed into the roof and he is hovering just above her. He smirks when the softest of noises escapes her lips as her back hits the tiles on the roof. He deepens the kiss breathing in the scent of seasalt and gunpowder on her skin. They break away from each other leaving both breathless and panting. She grabs onto his hands this time, squeezing tightly. She brings them up and places a chaste kiss to the tops of them. He gazes into her eyes searching for something that told him she enjoyed it, she sighs and his heart drops.

She must have seen the look in his face because her grip tightens and she entwines her fingers with his. "Alright Kenway." His head shoots up, eyes twinkling like the stars above. "We can try it, but if it don't work out," she winks at him and stands, nearly knocking him off the roof, "You're joining our creed." His hands tighten around hers tightly and he leans in to seel the words in a kiss. She turns her head and his lips land against her cheek, she winks at him playfully and hops from the roof to land in the haystack just below. He can't stop that ever growing smirk on his face, Well that could have gone a whole lot worse. He pulls his hood up and hops off, chasing after her.


	2. Day Nine: Hanging out with friends

_Parody fic ahead! I hope you enjoy!_

By mid afternoon he thought that no one would be coming, He had invited all of his best mates to his newly aquired cove for a small celebration after sinking a large slaver ship. He pouted in his office, sitting at that grand desk which would be fit for any king. He slammed his bottle of rum down and scratched furiously on the piece of parchment in front of him.

 _To my dear mates who have the misfortune of calling me friends,_

 _How dare you not come to share this victory with me._ _Don't_ _bother trying to find me because_ _I'm_ _leaving the Indies before you even_ _receive_ _this letter._

 _Regards,_

 _Kenway_

Edward jumps at the voice, marking a sharp line through the center of the page. "Don't ya think that's a bit childish? Beside it sounds like a six year old wrote that."

He quickly hides said letter under a pile of books and leans back in his chair, "I haven't the faintest of what you're talking about." She smirks and leans over the desk, her collar had been down today and Edward couldn't help himself when he looked down her shirt to stare at her cleavage. "My eyes are up here Kenway." His eyes flick up to connect with her own just as she pulls her collar up around her neck.

"Anyway, you're not making a very good host hiding yourself up in here. I think you've got some guests to mingle with." Edward shoots up out of his chair and darts to the window. Plastering himself against the pane like a good old puppy dog. She snickers to herself at the image and he whips around angrily with hands on his hips. "What's so funny Kidd?" She waves him off and walks from the room, "Nothing Kenway, come on."

Edward had been on his third bottle already. He was just so happy everyone had made it. Thatch had shown up hours after everyone else claiming that he had received the wrong cordinates. It didn't matter though, he already had more drinks in him than Kenway and Kidd combined. The group of friends grew bored and with all the rum in their system they couldn't remember who suggested it. But they decided that truth or dare would be a fun and very scandalous game to play.

"Vane, I dare you to play a song on your butt cheeks until one o' us guesses the song!" Vane growls at the blonde who just grins. "I ain't doing that Kenway, you can take your bloody games and shove them up your arse!" Kenway crosses his arms with a shite eating smirk, "Then you have to lick Rackham's smelly feet."

Rackham shoots his head off the table, slurring drunkenly, "Oy oy! My feet don't stink!" Anne waves a hand in front of her face, "I'd have to disagree, Jack." He pouts and she simply laughs, giving him a peck to the cheek. The group turn back towards Vane who had tried to sneak away during the argument. He tenses up when he hears Blackbeard shout, "Where do you think your going mate? I'll hold ya down if I have to!"

The surly pirate rolls his eyes and stomps back to the group, he bends down and begins to slap at his arse cheeks. _Pat-pata-pat-pat Pat-pat-pat-pat Pat-pata-pat-pat pat-pat-pat-pat_

Thatch hops from his chair excitedly, "Oh, Drunken sailor! That was an easy one! Do another!" Vane glares at the burly man and snarls, "Hell no! It's your turn! Truth or dare Thatch." Without think Thatch belts out, "Dare!" Vane grins evily, now was his time to give him a dare he surely couldn't complete. He crosses his arms across his chest and laugh, "I want to see you do four consecutive cartwheels."

The group around him gasps, surely Thatch would be licking Rackham's feet because there's no way in hell he could pull off that feat, Especially not with the amount of rum the man had been drinking. Thatch winks, "Easy, watch." The man stumbles to the open area below and the group crowds around the wall, to cheer him on.

Thatch tries and tries but every time he got half way through he would fall over. Finally, kicking his feet in the air he does four sloppy cartwheels, barely even making it off the ground. He walks triumphantly back up the the table and sits down, ripping a bottle from Vane's hand, "See, mate, easy as taking candy from a babe." Vane's eyebrow ticks comically. "I said cartwheels Thatch, not flail your damn legs!"

The man leans back, the chair creaking under his weight. "I did cartwheels!" Vane stands up, fists raised but Kidd pushes him back down in his chair, "Calm mate, just let 'em have the win this time." Vane huffs and grumbles, "Fine, your turn Thatch."

Thatch leers towards Kidd, looking him up and down, "Boy!" He points, "Truth or dare mate!" Kidd points at himself, "Me?" The man nods, grinning ear from ear. "I wasn't intending to play but truth I guess." Thatch's mouth drops open, "No! Ya have to pick dare!" Kidd laughs clearly amused, "It's called _truth_ or dare, not dare or dare. Now give me a truth so we can get on with it." Thatch purses his lips, now he'd have to think of something else because he wasn't expecting Jim to pick dare, he thought he had more balls than that...

He perks up quickly and leans forward, "I've never heard you talking about the lassies, do ya prefer men?" James' face flushes at the implication, he crosses his arms over his chest and looks away, whispering, "Aye, I like cock." The whole group goes to hooting, Thatch belts out laughter, Hornigold and Vane both look at each other horrified, Anne grins happily she clearly thought it was cute that her little Jim was gay, and Kenway? Kenway just smirked. Hornigold caught his smirk and couldn't help but to quirk his brow.

James, red in the face, looks quickly over to Hornigold, "Truth or dare Ben." He sighs and stands up, "Dare, though I was hoping if I was quiet I wouldn't have been picked." James bites his lip before winking, "I dare ya to let one of us shave one of yer, wiskers." His mouth drops open and he looks down at Rackham's feet, would it be worth it to just take the loss? He shakes his head and gags, no. "Jim you've such a smooth face, I want you to do it." Kidd smirks and pulls out his knife, setting quick work to the right side of his friends face.

Ben rubs his bare cheek with his hand, it'd been quite a long time since his whiskers found their home. He grumbles a curse under his breath and glares up at Kenway who was laughing. "Kenway, you're next, truth or dare?" Kenway grins and looks devilishly at Kidd, "Truth." Hornigold asks curiously, "You and Kidd seem awfully close, have you ever done things with each other?" Edward's eyes glaze over as if remembering something, finally he grunts out, "Only in dreams." He looks over towards the young pirate, who's face was almost the color of his bandana. They lock eyes and Kidd simply glares at him. Kenway smirks and looks to Anne, "Annie, truth or dare?"

"Dare." Thatch laughs loudly again, "The lass has more balls that Kidd and Kenway!" Edward rolls his eyes and gleams are Anne, "I dare you to give Kidd a lap dance." Kidd looks at him eyes wide and mouths a silent, 'I'll kill you.' Kenway winks as Anne stands, heading to her target. She sits on his lap facing him and grinds down softly against his lap. She places a kiss to his cheek and stands up, the group is disappointed thinking that was it.

She turns her back to Kidd then bends over, sticking her arse dangerously close to the organ Kidd had lacked. She rocks her hips up and down, gently grazing his lap. All Kidd can do is turn another violent shade of red and remain stiff. Thatch laughs and points to his lap, "Oi he really is gay! If that was me in his shoes I'd be hard as a boulder." Kidd rolls his eyes, "Aye, we've been over this, I prefer men."

Anne giggles and places a palm to Kidd's cheek. He looks up at her and she laughs, "Kidd, truth or dare?" Kidd sighs, "Well ya'll gave me a hard time when I picked truth, so I guess dare." Anne pulls James from his spot, pulling his arm gently to Kenway. "I dare you to kiss Edward." James flushes yet again and shakes his head, "No, I'd rather lick Rackham's hairy feet than kiss that mangey old man."

"Oy, I ain't that bad a kisser, now come 'er mate." Edward grips onto Kidd's coat pulling him forward. The two remained near millimeters apart, Edward's hot rum stained breath fanning over her face. Kenway smirked and that's when Kidd connected their lips.

All sounds melted away as his chapped lips smoothed over her soft ones. He smirked, he could tell by those lips that she was anything but female. If only the others knew. Kenway backs them up, the back of Kidd's knees hit the table and she lets out a strangled moan. She links her arms tightly around his neck and deepens the kiss. Teeth and tongues fighting for dominance, she wraps her legs tightly around his hips and he grinds into her. Forcing a wicked gasp from her abused lips. Anne breaks the two apart, "I said kiss him not fuck him. And that was Jim's dare not yers Edward!" She wacks him playful over the head and he leans back, leaving James wanting and panting on the table.

Thatch stands up, stretching his broad shoulders out, "Well it's starting to get weird now, I think I'm heading back to Nassau." Hornigold nods in agreement and the two men walk back to the dock. Vane stands and kicks at Rackham, "Let's go Jack!" He gets no response and decides to leave his friend. Anne winks at Kidd and slings Jack's arm over her shoulder dragging his drunken form away. Kidd and Kenway are the only two left as they stand in awkward silence.

Edward eventually finds himself back in between her legs, breath fanning over her face, "Well _Kidd_ It's just you and me now." Mary smirks up at the blonde pirate and pulls him into a loving kiss, securing her arms tightly around his neck. She feels his tongue lapping hopefully at her bottom lip, she allows him access but promptly bites his tongue when it enters.

He backs away from her, bringing his hands protectively to his face. She leans forward and smirks up at him, "That's for embarrassing me in front of our mates." She opens her legs a bit and winks up at him. She jumps off the table moments later and makes sure to ghost her fingers over the tent his pants. "You better find a sheath for the sword of yours Kenway." She makes her way to the dark manor, leaving Edward to stare stupidly after her. "I think I've found one!" He shouts and chases after her into the manor.


End file.
